Indian Journal of Traditional Knowledge

Vol 20(1), January 2021, pp 26-32

Phytochemicals and antioxidant activity of Sisymbrium irio L. seeds

T Hailu‡, R K Gupta$ & A Rani*,†
Department of Applied Chemistry, Delhi Technological University, Shahbad Daulatpur, Main Bawana Road, Delhi-110 042, India
E-mail: ‡temesgenhailu88@gmail.com, ‡rkg67ap@yahoo.com, †archnar8@yahoo.co.in
Received 26 November 2019; revised 01 May 2020

Sisymbrium irio (Family: Cruciferae) is used in Unani medicine. The qualitative and quantitative analysis showed the
presence of different types of bioactive secondary metabolites for like phenols, flavonoids, saponins, terpenoids, except reducing
sugar and cardiac glycosides. The antioxidant activity was checked by DPPH and ABTS free radical trapping methods by using
standards such as ascorbic acid and trolox. The methanol extract of the Indian variety of the seeds of Sisymbrium irio showed a
very high antioxidant activity. The major pharmacological bioactive chemical compounds identified in different solvent extracts of
Sisymbrium irio were characterized as: 2, 4-Di-tert-butylphenol, n-Hexadecanoic acid, 3’, 5’-Dimethoxyacetophenone,
γ -Tocopherol, Cholesterol, 1-Nonedecene, γ -Sitosterol, Ergot-5-en-ol, (3- Beta, 24R)-3- Methylcrotononitrile, 1, 2 -
Cyclopentadi-one, 1, 3 - Cyclohexanedione, 4-Isothiocyanato-1-Butene, Isosorbide, Sinapic acid methyl ester, 1, E-8, Z-10-
Pentadecatriene and 7-Tetradecenal, (Z) and GC-MS fatty acid composition of the cold pressed seeds oil of plant showed the
presence of major fatty acids such as: Linolenic acid (36.29%), Linoleic acid (17.99%), Oleic acid (12.58%), cis-11-Eicosanoic acid
(9.2%), Erucic acid (9.19%) and Palmitic acid (6.66%). The elemental analysis of the seeds showed the presence of magnesium,
calcium, strontium, titanium, chromium, manganese, copper, zinc, boron, aluminium, silicon, barium, iron, phosphorus, sodium,
potassium and lead.

Keywords: Antioxidant activity, Elemental analysis, GC-MS analysis, Phytochemicals, Sisymbrium irio L. seeds
IPC Code: Int. Cl.21 A61K 36/31, A61K 36/00, A61K 39/00. A01N 43/40, A61K 36/00

The medicinal plants are the foundation of effective
sources of bioactive compounds used as phytomedicines
& the chemical compounds obtained from these
therapeutic plants played vital role in the discovery of
novel drugs for the treatment of the various categories of
human, and animal diseases1. They contain various types
of secondary metabolites (phytochemicals) and these
phytochemicals perform many physiological activities in
humans and animals. The therapeutic plant Sisymbrium
irio L belongs to the family Cruciferae and is called
Khubakalan (Urdu), Asalio, Khubkalan; Khakasi,
Khakshi (Persian), khubkhala (Hindi), Khubah (Arabic)
and London Rocket/Rocket Mustard (Common names)
and is found in various parts of the world2. In 1980,
Vohora et al.3, investigated the seeds of Sisymbrium irio
L. Indian origin for antipyretic, analgesic and
antimicrobial activity. In 1991, Khan et al., isolated
isorhamnetin, quercetin, β-sitosterol and β-sitosterol-3
β-D-glucoside from aerial parts of the Sisymbrium irio
L. collected from the campus of Jamia Hamdard, New
Delhi, India4. The phytochemical and biological studies
(LD50, antioxidant activity) of the aerial part of Saudi
Arabia species (Najed Region) of Sisymbrium irio L.
—————
*Corresponding author
contained flavonoids5, β-sitosterol, stigmasterol and
β-sitosterol glucoside6. A research study on the
investigation of Baghdad-Iraq (Al-Jadrea) species of
Sisymbrium irio L. showed the presence of nicotine in
the aerial part of the plant7. Another study conducted on
the aerial part of the Sisymbrium irio L. collected from
the Irbid area (north of Jordan) showed the oil comprised
of four fatty alcohols (2.49%), five aromatic compounds
(3.53%), six aliphatic hydrocarbons (6.29%), fifteen
terpenes derivative (terpenoids) (8.19%), eleven sulfur
and eleven nitrogen containing compounds (36.41%),
two esters and seven acids (38.80%) and three additional
compounds (1.17%)8. Rauf and Ahmed9 reported fatty
acid distribution pattern in triacylglycerol (isolated from
oil) of S. irio. Another research study conducted by
Nengroo and Rauf stated the fatty acid composition of
petroleum extract of Sisymbrium irio L. seed were:
Palmitic acid C16: 0 (22.3%), Stearic acid C18:0 (6.1%),
Oleic acid C18:1 (30.7%), Linoleic acid C18:2 (30.3%),
Arachidic acid C20:0 (2.1%), Gondoic acid C20:1
(0.6%), Behenic acid C22:0 (0.5%), Erucic acid C22:1
(0.3%), Lignoceric acid C24:0 (0.3%), total unsaturated
fatty acids (61.9%) and total saturated fatty acids
(31.3%)10. The seeds of the Indian variety of
Sisymbrium irio L. contained isorhamnetin11 and is used
 HAILU et al.: PHYTOCHEMISTRYOF SISYMBRIUM IRIO L. SEEDS
as expectorant, febrifuge, rubefacient and are used
asthma, and in the preparation of poulties12. In 1998,
Guil et al.13, from Spain investigated the leaves of wild
edible Sisymbrium irio L. (Hedge Mustard) for
nutritional purposesbecause of the various amounts of
nutrients (protein 3.43%, carbohydrates 1.43%, lipid
2.14%, oxalic acid/Calcium ratio 1.1) and fatty acids ω3
(46.57%) & ω6 (13.02%) together with erucic acid
C22:1ω9 (2.52%). Ethanolic solvent extracts of fresh
plant of Sisymbrium irio L. seeds collected at flowering
stage from Peshawar University Campus, Pakistan
reported the cytotoxic, phytotoxic and insecticidal
activities14. Other Studies conducted on Indian variety of
ethanolic extract of Sisymbrium irio L., seeds on in vitro
rat mast cells has a significant broncho protective role in
mast cell degranulation induced by the compound 48/80
and active anaphylaxis15. In 2017, Gamal et al., from
Egypt reported the n-hexane extract of Sisymbrium irio
L. leaves collected from Bahariya Oasis, inhibited the
growth of microbial strains such as Staphylococcus
epidermidis and Klebsiella pneumoniae, whereas the n-
hexane extract of Sisymbrium irio L. seed demonstrated
greater inhibitory effect against Staphylococcus
epidermidis and Pseudomonas aeruginosa. The ethyl
acetate fraction of the leaves of Sisymbrium irio L. was
active against the gram-negative bacteria such as
Pseudomonas aeruginosa, Escherichia coli, Klebsiella
pneumoniae and the aqueous extract of Sisymbrium irio
L was active to against all tested pathogenic microbial
such as Klebsiella pneumoniae, Staphylococcus aureus,
Escherichia coli, Pseudomonas aeruginosa,
Enterococcus faecium, Acinetobacter baumanii,
Enterobacter cloacae and Candida albicans and the
purified compound showed dose dependent cytotoxic
activity against Vero cell line16. The various polarity-
based extracts of the seeds and leaves of Sisymbrium irio
L. collected from Islamabad and Rawalpindi showed
inhibition against the bacterial and fungal strains17. A
study conducted on aerial part of Sisymbrium irio L.
collected from Al-Jadriya area of Baghdad-Iraq declared
the methanol and ethyl acetate extract of the plant owns
hepatoprotective activity against CCl4 induced
hepatotoxicity in rats18. Research conducted on the
acute-toxicity, anti-inflammatory and bronchial smooth
muscles investigation of Indian variety of Sisymbrium
irio L. (seeds) is safe up to the doses of 1000 mg/kg and
caused no mortality and normal behaviour on the tested
animal19. In view of the significance of the plant, the
present investigation was conducted to carry out the
chemical examination, antioxidant and elemental
analysis of seeds of Indian variety of Sisymbrium irio L.
used in Unani medicine collected from Delhi.
27
Experimental Methods
Assortment and Documentation of the plant material
Seeds of Sisymbrium irio L. were obtained from
Khari Baoli, Delhi, Indian Drugs House. Botanical
specimens of the plant were identified by Dr. Mokhtar
Alam, Central Council for Research in Ayurvedic
Sciences, Ministry of Ayush, Government of India, New
Delhi and the voucher specimen/file number 6238 was
deposited at the Ministry of Ayush, Government of
India, New Delhi.
Preparation of extracts
The seed oil of Sisymbrium irio L. was extracted by
cold press machine, then 100 g of the powdered seeds
was extracted sequentially with the solvents of increasing
polarity viz; n-Hexane, Chloroform, Ethylacetate and
Methanol for 48 h on a rotary shaker. The extracts
obtained after extraction were filtered using Whatman
filter paper and concentrated on a rotary vacuum
evaporator.
Qualitative phytochemical tests
The qualitative phytoconstituents tests of Sisymbrium
irio L. extracts were done using standard procedures20-22.
Estimation of the total phenolic contents
The phenolic contents were estimated following
Folin-Ciocalteu index protocol23.
Estimation of the total flavonoid contents
The flavonoid contents were calculated according
to some modifications of Khalil et al.24.
DPPH free radical trapping activity
DPPH free radical trapping action of the solvent
extracts was carried with some modification25.
ABTS-scavenging analyses
The positive control such as trolox used for the
analyses ABTS-antioxidant activity of the extracts26.
Gas Chromatography-Mass Spectrometry analysis
Sisymbrium irio L. seeds extracts of n-hexane,
chloroform, ethyl acetate and methanol were injected in
GC-MS (Shimadzu GCMS-QP2010 Plus) for obtaining
the results. The samples were introduced in split mode at
300°C. The oven was heated from 40°C (1 min) to
300°C (28 min). The column flow rate was 1.21 mL/min
with Helium being the carrier gas. Metal quadrupole
mass filter with pre-rod with a range of m/z 1.5–1000
was used in scan mode. Electron Ionization (EI) was
used as the ionization mode. The bioactive
phytochemicals present in the extracts were identified by
means of their retention time and comparison of their
mass spectra with the National Institute of Standard and
Technology (NIST) library data and literature.
28 INDIAN J TRADIT KNOW, JANUARY 2021

Table 1 — Phytochemical investigation of Sisymbrium irio seeds extracts

Phytochemicals Test n-Hexane extract Chloroform extract Ethyl acetate extract Methanol extract
Flavonoids Alkaline test + + + ++
Phenols Ferric Chloride test + + + ++
-
Terpenoids Liebermann-Burchard test + + +
Reducing sugar Benedict’s test - - - -
Saponins Foam test - - + -
Cardiac glycosides Salkowski test - - - -
+ = the presence of phytochemicals - = the absence of phytochemicals
Preparation of fatty acid methyl esters
In order to make fatty acids present in the seeds oil
volatile, derivatization was done prior to GC-MS
analysis. Derivatized fatty acid methyl esters were
analyzed using a Shimadzu GC-2010.

Inductively Coupled Plasma-Mass Spectrometry (ICP-MS)

The seeds of Sisymbrium irio L. were milled,
homogenized and digested by microwave. The elemental
analysis of the sample was done by ICP-MS (Perkin
Elmer Sciex Elan II DRC).

Results and Discussion Fig. 1 — Total phenolic contents in different extracts of

Sisymbrium irio seeds
Phytochemical investigation of Sisymbrium irio L. seeds extracts
The qualitative phytochemical analysis showed the
presence of flavonoids and phenols in all extracts,
Terpenoids were found in chloroform, ethyl acetate
and methanol extracts, except n-hexane extract.
Saponins were only identified in the ethyl acetate
extract. Reducing sugar and cardiac glycosides were
not identified in any of the extracts (Table 1). The
phytochemical compounds in the plant parts were
recognized to be biologically active compounds and
they had been accountable for diverse activity, for
example, antimicrobial, antioxidant, antifungal and
anticancer27,28. The terpenoids show antiviral,
antibacterial, antimalarial, anti-inflammatory and Fig. 2 — Total flavonoid content in the seeds extracts of
anticancer activities29. The phenolic compounds are Sisymbrium irio
known for anti-microbial activity30, antiviral, Quantitative estimation of the total flavonoid contents
antimutagenic, antioxidant, antiinflammatory, Total flavonoids content varied from 8.958 ± 0.420
31-33
anticarcinogenic activities . to 13.266 ± 0.015 µg QE/mg of dry extract (Fig. 2).
Methanol extract contained the highest number of
Quantitative estimation of the total phenolic contents flavonoid contents, followed by chloroform and
Phenolic compounds widely distributed in plant parts n-hexane and ethyl acetate extracts. Unlike phenolic
are beneficial to human health due to their antioxidant contents, the ethyl acetate extract contained less
activity34,35. Quantitative estimation of the total phenolic amount of flavonoids as compared to other extracts.
contents varied from n-hexane extract to methanol
extract of Sisymbrium irio L. seeds ranging from DPPH radical scavenging activity
7.8 ± 0.278 to 55.3 ± 0.319 µg GAE/mg of dry extract We analysed the antioxidant activity test of extracts
(Fig. 1). Methanol extract contained the highest via DPPH (Diphenylpicrylhydrazyl) and ABTS (2, 2’-
percentage of total phenolic components, followed by Azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid)
ethyl acetate, chloroform and n-hexane extracts. test. Diphenylpicrylhydrazyl is a steady free radical
 HAILU et al.: PHYTOCHEMISTRYOF SISYMBRIUM IRIO L. SEEDS 29

compound & has an absorbance in its oxidized form radicals38. DPPH free radical scavenging activities of
to 515-520 nm36,37. Diphenylpicrylhydrazyl is seed extracts of Diphenylpicrylhydrazyl L extended
moderately fast & productive technique to assess free from 22.3% to 79.94%. The methanol extract showed
radical. The colour changes, from purple to yellow the highest percentage of free radical scavenging
demonstrates a decline in absorbance of DPPH activity as shown (Fig. 3) at the concentration of 1
radical. This is the confirmation of the interaction of mg/mL.
the antioxidant found in sample with the free ABTS radical scavenging assay
The solvent extracts of Sisymbrium irio L.
exhibited ABTS free radical scavenging activities
ranging from 43% to 94.3%. Out of all the extracts,
methanol extract as shown in (Fig. 4) contain the
highest percentage of free radical scavenging activity.
Gas Chromatography-Mass Spectrometry analysis of
Sisymbrium irio L. seeds extracts
The main constituents of the seeds extracts of
Sisymbrium irio L. identified by GC-MS as shown in
(Table 2) was found to be 2, 4-Di-tert-butylphenol, 3’,
Fig. 3 — % of free radical scavenging assay of seeds extracts of 5’-Dimethoxyacetophenone, n-Hexadecanoic acid,
Sisymbrium irio 7,10,13-Hexadecatrienal, 9, 12-Octadecadienoic acid
Table 2 — GC-MS analysis of bioactive compounds from seeds extracts of Sisymbrium irio
n-Hexane extract Chloroform Ethyl acetate Methanol
extract extract extract
Name of compounds R. time Area% Mol. formula M.wt Present/Absent Present/Absent Present/Absent Present/Absent
2,4-Di-tert-butylphenol 24.408 0.60 C14H22O 206 + + - -
3',5'-Dimethoxyacetophenone 25.668 0.55 C10H12O3 180 + + + +
n-Hexadecanoic acid 34.563 5.46 C16H32O2 256 + + + -
9,12-Octadecadienoic acid (Z, Z)- 38.060 37.57 C19H34O2 294 + - - -
9,12-Octadecadienoic acid (Z, Z)- 38.090 5.02 C19H26O2 280 + - - -
cis, cis, cis-7,10, 38.158 24.08 C16H26O 234 + - - -
13-Hexadecatrienal
γ -Tocopherol 51.491 3.26 C28H4802 416 + - + -
Cholesterol 52.383 1.91 C27H46O 386 + + + -
γ-Sitosterol 54.859 9.11 C29H50O 414 + + + +
1-Nonadecene 30.955 - C19H38 266 - - - -
1-Nonadecene 35.001 - C19H38 266 - + - -
(R)-(-)-14-Methyl-8-hexadecyn-1-ol 38.199 - C17H32O 252 - + + -
1-Heptacosanol 38.714 - C27H56O 396 - + - -
9,12,15-Octadecatrienoic acid, 46.689 - C19 H32O2 306 - - + -
ethyl ester, (Z, Z,)
Ergost-5-en-3-ol, (3. Beta, 24R)- 53.771 - C28H48O 400 - + + -
O-Ethyl S-2- 43.630 - C8H20NO2PS 225 - - + +
dimethylaminoethylethylphosphon
othiolate
3-Methylcrotononitrile 4.378 - C5H7N 81 - - - +
1,2-Cyclopentanedione 8.183 - C5H6O2 98 - - - +
4-Isothiocyanato-1-Butene 9.683 - C5H7NS 113 - - - +
1,3-Cyclohexanedione, 2-methyl 13.267 - C7H10O2 126 - - - +
4H-Pyran-4-one, 2,3-dihydro- 14.696 - C6H8O4 144 - - - +
3,5-dihydroxy-6-methyl
Isosorbide 19.042 - C6H10O4 146 - - - +
2-Butanone, 4-(2,6,6-trimethyl- 28.044 - C13H22O 194 - - - +
1-cyclohexen-1-yl)-
Sinapic acid methyl ester 36.682 - 238 C12H14O5 - - - +
1, E-8, Z-10-Pentadecatriene 37.581 - C15H26 206 - - - +
7-Tetradecenal, (Z) 37.701 - C14H26O 210 - - - +
30 INDIAN J TRADIT KNOW, JANUARY 2021

Table 3 — Fatty acid composition of Sisymbrium irio seeds oil

Peak No. Component Name Area (%)
1 C14 Myristic Acid 0.05
2 C15 Pentadecanoic Acid 0.03
3 C16 Palmitic Acid 6.66
4 C16: 1 Palmitoleic Acid 0.22
5 C17 Heptadecanoic Acid 0.07
6 C18 Stearic Acid 2.2
7 C18:1 Δ9 Oleic Acid 12.58
8 C18:2 Δ9, 12 Linoleic Acid 17.99
9 C18:3 Δ9.12.15Linolenic Acid 36.29
10 C20 Arachidic Acid 1.75
11 C20: 1 Cis-11 Eicosenoic Acid 9.2
12 C20: 2 Cis-11, 14 Eicosenoic Acid 0.95
Fig. 4— % of free radical scavenging essay of seeds extracts of 13 C20:3 Cis-11, 14, 17-Eicosatrienoic Acid 0.87
Sisymbruim irio 14 C22 Behenic Acid 0.63
15 C22:1 Erucic Acid 9.19
(Z,Z)-, γ-Tocopherol, Cholesterol, γ-Sitosterol, 16 C22:2 Cis-13, 16-Docosadienoic Acid 0.21
1- Nonadecane, 1-Heptacosanol, 3-Methylcrotonitrile, 17 C24 Lignoceric Acid 0.28
18 C24:1 Nervonic Acid 0.81
1,3-Cyclohexanedione, O-Ethyl S-2-dimethylaminoe-
thylethylphosphonothiolate, 1, 2-Cyclopentadiene, Table 4 — Mineral content of Sisymbrium irio seeds
Isosorbide, 4-Isothiocyanato-1-Butene, Sinapic S. No. Analyte Sample concentration (ppm)
acid ester, E-8, Z-10-Pentadecatriene, 9, 12, 1 Mg 2940.1
15-Octadecatrienoic acid, ethyl ester, (Z, Z, Z), 2 Ca 5844.7
7-Tetradecenal and (R)-(-)-14-methyl-8-hexadecyn-1- 3 Sr 18.2
4 Ti 7.7
ol. Phytochemical examination of the different extracts 5 Cr 2.6
namely n-hexane, chloroform, ethyl acetate and 6 Mn 41.8
methanol identified by GC-MS revealed the presence of 7 Co bdl
different types of phytochemicals and these compounds 8 Cu 5.5
may be responsible for various pharmacological 9 Ni bdl
activities such as hepatoprotective, antioxidant, wound 10 Zn 40.7
11 B 1.9
healing, and antimicrobial activities.
12 Al 315.4
13 Si 101.6
GC-MS fatty acid profile of Sisymbrium irio L. cold pressed seed oil
14 Ba 3.7
The major fatty acid composition of Sisymbrium irio 15 Fe 672.8
L. seed oil as shown in (Table 3) was found to be: 16 Mo bdl
Linolenic acid (36.29%), Linoleic acid (17.99%), Oleic 17 Ag bdl
acid (12.58%), cis-11-eicosenoic acid (9.2%), Erucic 18 P 6393.4
acid (9.19%), Palmitic acid (6.66%), Stearic acid (2.2%), 19 Na 54.7
Arachidic acid (1.75%) and cis-11, 14 Eicosenoic acid 20 K 8031.9
21 Pb 2.9
(0.95%). Linoleic acid (omega 6) is one of the 22 Bi bdl
fundamental fatty acids that are not created in the human 23 Cd bdl
body and should be given to the body from outside as 24 V bdl
such Sisymbrium irio L. seed oil is a good source of bdl: below detection limit
linoleic acid. Likewise, linoleic acid (omega 6) as a
were analyzed from Sisymbrium irio L. seed is very
metabolic precursor of eicosanoids which forms
useful for the health of human beings. The elements
important lipids like prostaglandins play an important
for example calcium, phosphorus and magnesium
role in inflammation, immunity and blood clotting.
may be helpful in the buildings of our bones;
Metal analysis of Sisymbrium irio L. seeds (ICP-MS) potassium and sodium support in the preservation of
Elemental analysis of Sisymbrium irio L. seeds normal blood pressure. The metal iron is the centre of
showed the existence of various types of minerals in haemoglobin and a part of myoglobin. During
different concentration (Table 4). The minerals which breakdown of carbohydrates, fats and proteins the
 HAILU et al.: PHYTOCHEMISTRYOF SISYMBRIUM IRIO L. SEEDS
elements copper, zinc and manganese play important
roles. During the metabolic processes of bone, the
elements such as zinc, manganese and copper serves
as cofactors for specific enzymes39.
Conclusions
Phytochemical analysis of the different extracts
of the Indian variety of Sisymbrium irio L.
seeds revealed the presence of phenols, flavonoids,
terpenoids, saponins, and other bioactive
metabolite including 2, 4-Di-tert-butylphenol, 3’, 5’-
Dimethyoxyacetophenone, 9, 12-Octadecadienoic
acid (Z,Z)-, n-Hexanoic acid, cis, cis, cis-7, 10,
13-Hexadecatrienal, γ-Tocopherol, Cholesterol,
γ-Sitosterol, 1-Heptacosanol, 1,3-Cyclohexanedione,
O-ethyl-S-2-dimethylaminoethylethylphosphonothioate,
3-Methylcrotonitrile, 1,2-Cyclopentadiene, 4-Isothio-
cyanato-1-Butene, Isosorbide, Sinapic acid ester, 7-
Tetradecenal, 9, 12, 15-Octadecatrienoic acid, ethyl
ester(Z, Z, Z) and (R)-(-)-14-methyl-8-hexadecyn-1-ol.
The major fatty acid profile of Sisymbrium irio cold
pressed seed oil contained, Linolenic acid (36.29%),
Linoleic acid (17.99%), Oleic acid (12.58%), cis-11-
Eicosenoic acid (9.2%), Erucic acid (9.19%), Palmitic
acid (6.66%), Stearic acid(2.2%), Arachidic acid
(1.75%) and cis-11, 14-Eicosenoic acid (0.95%). The
significant antioxidant activity of Sisymbrium irio L
seed and its frequent use in Unani medicine prompted us
to investigate this seed material of our Indian variety.
There is need to validate the claims for its usage by
investigating the biological activities of purified
compounds and to develop a new drug candidate based
on Unani system of medicines.
Acknowledgement
Temesgen Hailu wishes to show gratitude towards
the Delhi Technological University, Delhi, India has
Delhi, India.
Conflict of Interest
The authors express no conflict of interest
Author Contributions
T Hailu is a PhD student from the Delhi
Technological University, Delhi, India has carried out
all the experiments related to this manuscript. R K
Gupta (co-supervisor) & A Rani (supervisor) have
contributed in the manuscript writing and
conceptualization of the work done.
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